Literature DB >> 17346060

An efficient waste-free oxidative coupling via regioselective C-H bond cleavage: Rh/Cu-catalyzed reaction of benzoic acids with alkynes and acrylates under air.

Kenji Ueura1, Tetsuya Satoh, Masahiro Miura.   

Abstract

[structure: see text]. The direct oxidative coupling of benzoic acids with internal alkynes proceeds efficiently in the presence of a rhodium/copper catalyst system under air to afford the corresponding isocoumarin derivatives. The reaction forms no wastes except for water. Under similar conditions, the aerobic coupling with acrylates also takes place smoothly to produce 7-vinylphthalide derivatives via divinylation and subsequent cyclization.

Entities:  

Year:  2007        PMID: 17346060     DOI: 10.1021/ol070406h

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  38 in total

1.  Recent advances in the synthetic and mechanistic aspects of the ruthenium-catalyzed carbon-heteroatom bond forming reactions of alkenes and alkynes.

Authors:  Chae S Yi
Journal:  J Organomet Chem       Date:  2011-01-01       Impact factor: 2.369

2.  Rh(III)-Catalyzed C-H Bond Addition/Amine-Mediated Cyclization of Bis-Michael Acceptors.

Authors:  Tyler J Potter; Jonathan A Ellman
Journal:  Org Lett       Date:  2016-07-20       Impact factor: 6.005

3.  Cobalt-Catalyzed Coupling of Benzoic Acid C-H Bonds with Alkynes, Styrenes, and 1,3-Dienes.

Authors:  Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-10       Impact factor: 15.336

4.  Correlating Reactivity and Selectivity to Cyclopentadienyl Ligand Properties in Rh(III)-Catalyzed C-H Activation Reactions: An Experimental and Computational Study.

Authors:  Tiffany Piou; Fedor Romanov-Michailidis; Maria Romanova-Michaelides; Kelvin E Jackson; Natthawat Semakul; Trevor D Taggart; Brian S Newell; Christopher D Rithner; Robert S Paton; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2017-01-06       Impact factor: 15.419

5.  Ether-directed ortho-C-H olefination with a palladium(II)/monoprotected amino acid catalyst.

Authors:  Gang Li; Dasheng Leow; Li Wan; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2012-12-13       Impact factor: 15.336

Review 6.  Electronic and Steric Tuning of a Prototypical Piano Stool Complex: Rh(III) Catalysis for C-H Functionalization.

Authors:  Tiffany Piou; Tomislav Rovis
Journal:  Acc Chem Res       Date:  2017-12-22       Impact factor: 22.384

7.  Rh(III)-catalyzed oxidative coupling of unactivated alkenes via C-H activation.

Authors:  Andy S Tsai; Mikaël Brasse; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2010-12-22       Impact factor: 6.005

8.  Stereodivergent Rhodium(III)-Catalyzed cis-Cyclopropanation Enabled by Multivariate Optimization.

Authors:  Tiffany Piou; Fedor Romanov-Michailidis; Melissa A Ashley; Maria Romanova-Michaelides; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2018-07-23       Impact factor: 15.419

9.  Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.

Authors:  Marc Presset; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  Org Lett       Date:  2013-03-15       Impact factor: 6.005

10.  Mechanistic study of the oxidative coupling of styrene with 2-phenylpyridine derivatives catalyzed by cationic rhodium(III) via C-H activation.

Authors:  Mikaël Brasse; Juan Cámpora; Jonathan A Ellman; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2013-04-16       Impact factor: 15.419

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